A beautiful character is punished by being turned ugly, which is a Fate Worse than Death. Usually a punishment for vanity, but not necessarily. See also Beauty to Beast, which is the general trope of a beautiful person turning ugly for whatever reason, including plain old-fashioned aging.
- Inverted for one story arc of Deadpool: The normally hideous merc is cursed... into looking like Thom Cruz. Otherwise played exactly straight, as it was an effective punishment — he explains that he has no problem with looking pretty, and he even wants to look pretty, but he wants to look pretty himself. He doesn't want someone else's face.
- In Generation X, Monet St. Croix was turned into the freakish Penance by her evil big brother as a punishment for her vanity.
- In the first issue of Seven Soldiers of Victory: Frankenstein, teenage outcast Uglyhead forges an alliance with the Sheeda to get revenge on his classmates. To this end, one of the girls who made fun of him is forced to accept a Sheeda spine-rider, who forces her to eat herself into obesity.
- The Morlock Masque from X-Men comics does this to victims with his (later her) mutant powers; because Masque can't (initially) use their powers to make their own ugly face handsome, they take it out on others by deforming their appearance.
- In the first arc of X-Statix, the team deals with a disfigured teenage Reality Warper who has used his powers to make almost everyone else in his hometown hideous in revenge for a bunch of kids beating him so badly that he had to be hospitalized.
- In one Peanuts strip, Peppermint Patty supposed that her ugliness was a punishment for something she had done in a previous life.
- In The Final, this is how Heather and Bridget, the Alpha Bitches at the high school, are tortured by the outcasts: Emily smears a flesh-eating chemical goo onto their faces in order to destroy their good looks. The prologue and epilogue reveal that, afterwards, Bridget became an outcast herself as a result, with her hiding her scarred face under a hoodie and her hair.
- In Freaks, when the titular circus freaks learn that the conventionally beautiful Cleopatra plans to marry and kill one of them for his money, they mutilate her to make her a freak just like them. Also counts as a Karmic Transformation, since Cleopatra had been disdainful of the freaks for how ugly they were.
- In Friend Request, Laura is the prettiest and most popular girl in her college who takes pity on an unpopular girl, Marina, and accepts her friend request. After Laura unfriends Marina because of her stalking and harassment, Marina kills herself, and her spirit haunts and torments Laura and her friends in revenge. Marina seeks to particularly punish Laura by destroying her life and popularity, with one of the methods being the destruction of Laura's beauty. Laura discovers that her face has began to deteriorate and become increasingly gaunt, and soon sees that she has lost some of her good looks and is no longer the prettiest girl in the school. As time progresses while Marina torments Laura and her friends, Laura's face continues to gradually deteriorate and she continues to lose her good looks, and eventually she is no longer beautiful. Laura manages to stop Marina, but as seen in the last scene,this results in Laura being terribly and permanently disfigured. Her face is ruined, she will never be beautiful again, she has become the ugliest girl in the school, and she has lost all her popularity and become an outcast.
- In Irréversible, the stunningly beautiful Alex is permanently disfigured after a sadistic pimp beats her face in to destroy her physical beauty. Alex's face is ruined by the beating, and she will likely never be beautiful again.
- In the film Penelope (2006), the title character is "cursed" to have a pig nose. People tend to respond to her looks extremely negatively.
- In Se7en, the Pride kill has John Doe cutting up the face of a beautiful but vain woman and making her choose between suicide and life with an ugly face. She chooses suicide.
- Spaceballs: After kidnapping Princess Vespa, the villains give an ultimatum to her father, threatening to undo her nose job if he doesn't reveal the air dome's combination. Although Vespa herself pleads with him not to, he eventually caves, averting this trope.
- In When Evil Calls, the gorgeous Victoria becomes disfigured due to her vanity and cruel behavior toward Jane. Victoria humiliates Jane when she pushes her aside without a second look because she does not find her attractive enough to even acknowledge, pointedly praises Samantha's looks, and walks away with Samantha without looking back. In the lab she sneers at the teacher's warning to be careful with the acid and doesn't want to wear goggles to mess up her makeup. She then laughs when Kirsty reads Jane's wish that she was prettier than Victoria and Kirsty calls her ugly. This leads to an upset Jane pushing Kirsty, who then crashes into Daniel, who then falls forward and accidentally releases the acid in his beaker onto Victoria, which is able to completely spread across her face because she was not wearing goggles. The acid quickly ravages Victoria's face and destroys most of her features and all of her beauty. Jane's wish is fulfilled and she is much prettier than the now horrifyingly ugly Victoria.
- The book Beastly is a modern version of "Beauty and the Beast". Protagonist Kyle is a rich jerk who embarrasses Kendra, an unpopular girl who turns out to be a witch. He gets cursed by turning into a hideous beast, until he receives True Love's Kiss. In the book, at least. In the movie, he just gets cursed into looking like a member of the Jim Rose Circus.
- Beauty and the Beast is the most obvious, with the Beast having been transformed into a grotesque monster in punishment for failing the Old Beggar Test.
- In "The Case of Lady Sannox" by Arthur Conan Doyle, Lady Sannox, known for her great beauty, has an affair with the surgeon Douglas Stone. He is tricked into horribly disfiguring her by her husband, who believes it will be morally good for her.
- In Dying Earth, the witch Javanne cursed her lover by making him hideously ugly; at the end of that story, she's forced to bring him before a god of justice, who decides a little Laser-Guided Karma is in order.
- In Homecoming Braelin Janquay is turned into a drider by the priestesses of House Melarn. What makes this worse, is that driders are outcasts of drow society, not only ugly but reviled by the populance. And the process of turning into one is so incredibly painful that all driders start out with memories of their torment and former lives wiped, because they couldn't stand living otherwise.
- In the first book of A Series of Unfortunate Events one of Olafs henchmen grabs Violet by her face and says she better not do anything to anger Olaf or he will ruin her pretty face as punishment.
- In the final book of The Wheel of Time, Graendal, formerly one of the world's greatest beauties, is punished for her counterproductive Chronic Backstabbing Disorder by being killed and reincarnated as a hideous, deformed old crone. As a Psycho Psychologist with horrific Mind Control powers, she promptly starts forcing her victims to see her new form as the highest ideal of beauty.
- An episode of Sabrina the Teenage Witch has a variation: During a particularly vain phase, Sabrina meets a kindhearted and charitable (according to Hilda and Zelda) yet ugly relative (her skin is spotted green) whom Sabrina treats with apprehension. Said relative decides to teach her a lesson...by gradually turning Sabrina's boyfriend Harvey into a werewolf-esque creature (so much for kindhearted). She changes Harvey back only when Sabrina accepts him despite his looks.
- In "The Masks", a fifth-season episode of The Twilight Zone (1959), a wealthy dying man summons his family to his New Orleans home for Mardi Gras. Since they're all grasping creeps waiting for him to die so that they'll inherit, he makes it a condition of his will that they wear grotesque masks matching their personalities until midnight. He dies at midnight and they take off their masks to find that their faces have been permanently molded into those shapes.
- The Greek mythical monster Medusa, who was so ugly that anyone who beheld her face was turned to stone, was supposedly afflicted with this. In many versions of the myth, she was originally a beautiful girl, but made the mistake of being raped by Poseidon in Athena's temple (or in more family-friendly versions, bragging about being more beautiful than Athena). Athena really didn't take it too well.
- According to some Midrashic interpretations of the Book of Esther, Vashti wasn't an innocent victim. Rather, she was vain, arrogant, haughty, narcissistic, and all around just a terrible, mean person that imposed extreme work on her (mostly Jewish) servant girls even on the Sabbath, and made them eat unkosher food. And the real reason she refused her husband's summons was not because she didn't want to parade naked before a bunch of drunk guys, but because God had finally had enough of her shit and sent an angel to punish her with some type of embarrassing disfigurement, often said to be the sudden and unexplained growth of a penis. However, it's important to note that the actual story supports none of this: the only "bad" thing Vashti did in the text was to refuse her husband's summons, which was viewed as treason by her patriarchal society.
- Taako of The Adventure Zone sacrifices his elven beauty during the Suffering Game arc. Downplayed slightly in that he only becomes average-looking, and immediately casts ''disguise self'' to make himself look like his past self.
- Part of the Dragonlance backstory has the Irda, a beautiful, powerful race of blue-skinned humanoids who were the first sentients created on Krynn who enslaved first the elves, than men when they proved more useful as laborers. After growing too arrogant, all but one clan (who were friendly to humans) were cursed by the gods and become the hideous green-skinned monsters known as Ogres.
- One very harsh example in Rocket Age. Although this might have been a side effect of the viral and nuclear bombardment of Io by the Europans, the Iotes went from being described as the most beautiful species in the solar system to looking like disease ridden, mutated dog men. Knowing the Europan's track record, they probably didn't even do anything to deserve it.
- In Vampire: The Masquerade, the Nosferatu Clan often Embraces vain, beautiful people, cursing them into looking like them. Depending on the individual vampire's tastes, this is done for two reasons: Some do this to teach "The Beautiful Elite" a lesson in humility, while others like to do this just so they can watch models and actors writhe in agony. Unfortunate victims of this kind of 'lesson' are dubbed "Cleopatras", allegedly after the character in Freaks.
- It's likewise believed that the Clan's founder, Absimiliard, was one of the most beautiful (and vain) of all the antediluvians, conspiring to murder his second-generation sire because she'd scratched his perfect face during his Embrace. When he went through with it, Caine made things much, much worse.
- In Vampire: The Masquerade Bloodlines, at least two members of the LA brood are (or were) Cleopatras: A supermodel named Imalia (who hasn't gotten over it), and a former silent movie star and their current primogen "Gorgeous" Gary Golden (who has gotten over it, considering he is Imalia's Sire).
- The Tzimisce do it on occasion as well, given that they've got Vicissitude. There's a NPC in the Mexico City book who made the mistake of pissing off Sascha Vykos; Vykos sealed up all his orifices, then Embraced him. The man has to chisel his eyes and mouth out on a nightly basis.
- In Into the Woods, the ugly old witch was really a beautiful woman who had been victim of this.
- This is how you permanently defeat S.M.A.S.H.'s Super Agent Mariana Mamba in Evil Genius, as she uses her sexiness to cause your minions to desert you (simply reducing her health bar to zero forces Super Agents to leave only temporarily). The exact details involve capturing her, then performing plastic surgery to make her fat and ugly.
- Inverted in King's Quest IV where the ugly, but good hearted Igor-like Edgar is turned into a Prince Charming by the fairy Genesta for his part in helping the Heroine. Though a later Retcon made it so that was his original form.
- In Metal Gear Solid 4, Snake apparently thinks of his Rapid Aging as this.
- In Runaway: A Road Adventure, Gina is captured and questioned by Gustav and Feodor, who work for some powerful criminals, because they (correctly) suspect she knows where a small fortune is hidden. Although they only want answers, their threats really play up on the fact that Gina is pretty and that if she won't talk that's what going to get some changing.
- In Vampire: The Masquerade Bloodlines, as in the tabletop game, the Nosferatu sometimes inflict their Looks Like Orlok variety of undeath on vain beauties to take them down a notch. One Nosferatu, Imalia, is a former top supermodel... who will pay handsomely to have her Unknown Rival successor's life ruined, suggesting that the lesson in humility didn't stick. (Justified, in that she's a Fledgling, a newly turned vampire.)
- Kavonn of Charby the Vampirate cursed a female character with a reactive version of this: She switches between beautiful and ugly depending on her actions. However the "ugly" form also comes with claws and strength, so she sometimes weaponizes it.
- Parodied in The Simpsons, when Homer is taking an oath when he becomes a Stonecutter.
Homer: And by the sacred parchment, I swear that if I reveal the secrets of the Stonecutters, may my stomach become bloated and my head be plucked of all but three hairs —
Moe: Um, I think he should have to take a different oath.
- In The Smurfs episode "The Tear of a Smurf", Chlorhydris' daughter Priscilla was a young woman punished by her mother by being turned into an old hag, and she seeks the tears of a Smurf for her formula to restore her youth.
- In the Visionaries episode "The Overthrow of Merklynn", Darkstorm does this to Virulina, after she, Lexor and Reekon make it known that they are not happy with his rule. Using the magic he has stolen from Merklynn, he turns her into an aged crone, then conjures up a mirror so that she can see what she now looks like.
Virulina: It is hideous! You have ruined my face!
Darkstorm: No, Virulina. I merely made your appearance match your soul.